For a laid-back look with a clear fashion twist, try teaming a black barn jacket with a crew-neck t-shirt. When not sure about what to wear when it comes to shoes, stick to navy and white canvas low top sneakers. When leaves are falling down and temperatures are falling, you'll appreciate how ideal this outfit is for awkward transition weather. Gentlemen wondering how to sport edgy casual dressing as you move into your 30s, this outfit should answer your question.